4-{[(1S,2S,5S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-4-oxobutanoic acid

• ChemBase ID: 6121
• Molecular Formular: C25H38O5
• Molecular Mass: 418.56622
• Monoisotopic Mass: 418.27192432
• SMILES: C1C[C@H](OC(=O)CCC(=O)O)C[C@@H]2CC[C@@H]3[C@@H]([C@@]12C)CC[C@]1([C@H]3CC[C@@H]1C(=O)C)C
• Canonical SMILES: O=C(O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C)CCC(=O)O
• InChI: InChI=1S/C25H38O5/c1-15(26)19-6-7-20-18-5-4-16-14-17(30-23(29)9-8-22(27)28)10-12-24(16,2)21(18)11-13-25(19,20)3/h16-21H,4-14H2,1-3H3,(H,27,28)/t16-,17-,18-,19+,20-,21-,24-,25+/m0/s1
• InChIKey: UVTGFMKBPVLATL-DSOJQRAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S,2S,5S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{[(1S,2S,5S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-4-oxobutanoic acid
• Synonyms: 5-ALPHA-PREGNANE-3-BETA-OL-HEMISUCCINATE

Database IDs

• PubChem SID: 160969546; 99444981
• PubChem CID: 5289324

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.110753
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.8494415
• LogD (pH = 7.4): 1.1607773
• Log P: 4.252926
• Molar Refractivity: 112.9515 cm^3
• Polarizability: 45.22449 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.37
• LOG S: -5.38
• Solubility (Water): 1.75e-03 g/l

DETAILS

DrugBank - DB08510

Drug information: experimental